Trichloroisocyanuric Acid → HCID 67172499, compound

HRID 1506557Notes

Reaction equation

HRID 1506557 reaction equation
[OH:1][CH:2]([C:7]1[CH:8]=[C:9]2[C:32](=[CH:33][CH:34]=1)[C:13]1=[N:14][O:15][C:16]([C:17]3[C:21]([C:22]([F:25])([F:24])[F:23])=[C:20]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:19][N:18]=3)=[C:12]1[CH2:11][CH2:10]2)[C:3]([O:5][CH3:6])=[O:4].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.CC1(C)N([O])C(C)(C)CCC1>ClCCl>[O:1]=[C:2]([C:7]1[CH:8]=[C:9]2[C:32](=[CH:33][CH:34]=1)[C:13]1=[N:14][O:15][C:16]([C:17]3[C:21]([C:22]([F:23])([F:25])[F:24])=[C:20]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[O:19][N:18]=3)=[C:12]1[CH2:11][CH2:10]2)[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 67171991HCID 67171991, compound

Product 1

HCID 67172499HCID 67172499, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetate (Preparation 134A, 260 mg, 0.55 mmol) in dichloromethane (5 mL) was added 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (193 mg, 0.83 mmol). The reaction mixture was stirred for 5 min. at room temperature. The reaction mixture was cooled to 0° C. and TEMPO (12.95 mg, 0.083 mmol) was added. The reaction mixture was warmed up to room temperature and was stirred for 1 h. The layers were separated and the organic phase was washed with sat. aq. sodium bicarbonate (5 mL) followed by 1N hydrochloric acid (5 mL) and brine (5 mL). The organic layer was dried and concentrated to provide methyl 2-oxo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetate (250 mg, 0.53 mmol, 97% yield): LC/MS M+1=470.02; 1H NMR (400 MHz, CDCl3) δ ppm 8.16-8.22 (1H, m), 8.01-8.08 (2H, m), 7.77 (2H, d, J=7.48 Hz), 7.53-7.68 (3H, m), 4.03 (3H, s), 3.15 (4H, s).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureThe reaction mixture was warmed up to room temperature
  3. stirringwas stirred for 1 h
  4. customThe layers were separated
  5. washthe organic phase was washed with sat. aq. sodium bicarbonate (5 mL)
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a528987ed2b141e088d80fc5b16445b7
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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